I will give you my opinion on the items I can relate to.
#1: No! (I won't sugar coat this, just being honest) A class 8 truck usually runs 12,000 plus front axle and 20,000 rears. Unloaded it is going to shake the hood and the dash and anything else in the truck when you hit rough roads. This is why they run air chairs and air cabs to at least keep the driver as comfy as possible. Run the truck fully loaded like it is meant to and it will ride like a caddy. When I bought my FLD 4 years ago and bobtailed it around I was very disappointed in the ride. I was really worried that is was going to ride that bad once I had my conversion on and I was bummed. I did add Broc's air ride system to the front axle and that did help, but the truck still rode rough. Once I put my conversion on which added 18,000 plus pounds to the chassis it rode great. In your application with the small trailer it is going to ride like a class 8, and I would not assume it will ride like a dually, I have had both. (Not sure from the info you provided above if you are thinking about pulling a fifth wheel RV or put a motorhome conversion)
As far as noise. You have to love the sound of a real diesel motor and the whistle of the turbo. If you do your gonna love a class 8! They are noisy, newer trucks are much better, but if your sitting on 11 plus liters of iron it rumbles like a freight train under throttle and you always have the whistle of the turbo. If you love that and your wife doesn't well, you maybe want to reconsider, although you may not hear her complaining.
I really recommend that you get into a Class 8 with the wife and take a spin, and for the most part they will all ride about the same. They all sit on pretty much the same chassis, big difference being front axle rating.
Truck makes will get as heated a debate as the pickups get. Some swear by KW or Pete, but I have talked with alot of truckers and most of them like the FL ride & ergo of the cab (newer versions), they just don't look as cool. And sometimes it better to look good than feel good.
#2: Yes & No My Cummins M11 & Fuller 10 speed got me 11 mpg with my conversion (weight was approx 33,000 with car jeep in tow) So yes with a pre-emissions motor, but with the newer emission motors I don't know if that is still possible.
#3: Duke it out!
#4 or 5: The big issue with lowering is that your gonna need room for the overhang past the back axles. If you have a 10' overhang you will be o.k. with current chassis height in 95% of all situations. The longer you go the worse you will drag. The lower the trucks ride height and you will need to shorten this overhang.
#6: With 36' box you will need tandems. Depending on truck and cab config most anything over 30' will require tandems do to wheel base issues. Keep your wheel base under 300" if at all possible and you can get around pretty well. My last conversion was 336" and it was completely miserable to maneuver. I am not saying it can't be done, but I am telling you from personnel experience DON'T DO IT! My current conversion is 295" and it is like night and day.
#7: If you like running in the winter, than aluminum might be your best bet. Most conversion companies use a steel frame rust proofed with galvanized boxes. Hit salt once or twice and the rust will start even if your good about flushing the chassis after salty travel. I am constantly painting and cleaning the chassis to keep this under control.
#8: Most run 96", not sure if Kingsley is 102 or not. If it gets laid over its done anyway, you just want it so if it does happen you can walk away.
#9: The good ones cut the frame at the center point of the current chassis from back of cab to end of rails, add in the stretch, butt weld, and than add a solid new c channel over the stretched rails from cab back which is bolted in place. Don't go cheap here, I have seen a few bent chassis when this is not done right.
#10: Your gonna want levelers, air bags are not going to be enough unless you hang out at the top resorts with super level parking spaces.
#11: Under box out the side, definitely want mufflers! Loud pipes don't save lives when they resonate under the conversion box. You could run some shorty stacks behind the cab if you like black sooty exhaust streaks down the side of your conversion box. I have seen one where they had fackey stacks and the real exhaust out the bottom. to much trouble for me.
Great questions!
Bill